DE2560074C2 - Verfahren zur Gewinnung von Clavulansäure und deren Salze - Google Patents
Verfahren zur Gewinnung von Clavulansäure und deren SalzeInfo
- Publication number
- DE2560074C2 DE2560074C2 DE2560074A DE2560074A DE2560074C2 DE 2560074 C2 DE2560074 C2 DE 2560074C2 DE 2560074 A DE2560074 A DE 2560074A DE 2560074 A DE2560074 A DE 2560074A DE 2560074 C2 DE2560074 C2 DE 2560074C2
- Authority
- DE
- Germany
- Prior art keywords
- clavulanic acid
- salt
- solution
- water
- percent
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- HZZVJAQRINQKSD-UHFFFAOYSA-N Clavulanic acid Natural products OC(=O)C1C(=CCO)OC2CC(=O)N21 HZZVJAQRINQKSD-UHFFFAOYSA-N 0.000 title claims description 220
- 229960003324 clavulanic acid Drugs 0.000 title claims description 218
- HZZVJAQRINQKSD-PBFISZAISA-N clavulanic acid Chemical compound OC(=O)[C@H]1C(=C/CO)/O[C@@H]2CC(=O)N21 HZZVJAQRINQKSD-PBFISZAISA-N 0.000 title claims description 204
- 150000003839 salts Chemical class 0.000 title claims description 64
- 238000000034 method Methods 0.000 title description 49
- 238000004519 manufacturing process Methods 0.000 title description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 112
- 239000000243 solution Substances 0.000 claims description 100
- 239000000706 filtrate Substances 0.000 claims description 55
- 239000002904 solvent Substances 0.000 claims description 41
- 150000002148 esters Chemical class 0.000 claims description 38
- 235000015097 nutrients Nutrition 0.000 claims description 36
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 27
- 239000002253 acid Substances 0.000 claims description 22
- 239000002609 medium Substances 0.000 claims description 18
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 17
- 241001233037 catfish Species 0.000 claims description 16
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 14
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 239000007788 liquid Substances 0.000 claims description 12
- 241000187747 Streptomyces Species 0.000 claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims description 11
- 239000012141 concentrate Substances 0.000 claims description 11
- 238000001914 filtration Methods 0.000 claims description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
- 230000007935 neutral effect Effects 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 10
- 239000001963 growth medium Substances 0.000 claims description 10
- 239000012043 crude product Substances 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 9
- 239000008055 phosphate buffer solution Substances 0.000 claims description 9
- 239000007864 aqueous solution Substances 0.000 claims description 8
- 229910052801 chlorine Inorganic materials 0.000 claims description 8
- 239000000725 suspension Substances 0.000 claims description 8
- 239000003957 anion exchange resin Substances 0.000 claims description 7
- 239000008346 aqueous phase Substances 0.000 claims description 6
- 229910000019 calcium carbonate Inorganic materials 0.000 claims description 6
- 239000003456 ion exchange resin Substances 0.000 claims description 6
- 229920003303 ion-exchange polymer Polymers 0.000 claims description 6
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 claims description 5
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 5
- 239000012266 salt solution Substances 0.000 claims description 5
- 230000002378 acidificating effect Effects 0.000 claims description 4
- 239000012876 carrier material Substances 0.000 claims description 4
- 239000012074 organic phase Substances 0.000 claims description 4
- 238000005191 phase separation Methods 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 3
- 239000011737 fluorine Substances 0.000 claims description 3
- 229910052731 fluorine Inorganic materials 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- 150000003335 secondary amines Chemical class 0.000 claims description 3
- 125000004434 sulfur atom Chemical group 0.000 claims description 3
- 150000003512 tertiary amines Chemical class 0.000 claims description 3
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 claims description 2
- ZPWVASYFFYYZEW-UHFFFAOYSA-L dipotassium hydrogen phosphate Chemical compound [K+].[K+].OP([O-])([O-])=O ZPWVASYFFYYZEW-UHFFFAOYSA-L 0.000 claims description 2
- 229910000396 dipotassium phosphate Inorganic materials 0.000 claims description 2
- 235000019797 dipotassium phosphate Nutrition 0.000 claims description 2
- 229910017053 inorganic salt Inorganic materials 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 238000012258 culturing Methods 0.000 claims 2
- 150000008043 acidic salts Chemical class 0.000 claims 1
- 238000005571 anion exchange chromatography Methods 0.000 claims 1
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 132
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 126
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 75
- 239000000203 mixture Substances 0.000 description 71
- -1 hydrocarbon radical Chemical class 0.000 description 68
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 57
- 159000000000 sodium salts Chemical class 0.000 description 53
- 230000005764 inhibitory process Effects 0.000 description 52
- 239000007787 solid Substances 0.000 description 51
- 230000002829 reductive effect Effects 0.000 description 46
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 45
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 40
- JGSARLDLIJGVTE-MBNYWOFBSA-N Penicillin G Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)CC1=CC=CC=C1 JGSARLDLIJGVTE-MBNYWOFBSA-N 0.000 description 33
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 32
- 238000012360 testing method Methods 0.000 description 32
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 30
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 26
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 24
- 239000003153 chemical reaction reagent Substances 0.000 description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 22
- 239000003054 catalyst Substances 0.000 description 21
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 20
- 238000010790 dilution Methods 0.000 description 20
- 239000012895 dilution Substances 0.000 description 20
- 239000012071 phase Substances 0.000 description 20
- 239000000741 silica gel Substances 0.000 description 20
- 229910002027 silica gel Inorganic materials 0.000 description 20
- 239000011780 sodium chloride Substances 0.000 description 20
- 230000000844 anti-bacterial effect Effects 0.000 description 19
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 18
- 239000003921 oil Substances 0.000 description 18
- 235000019198 oils Nutrition 0.000 description 18
- 239000000126 substance Substances 0.000 description 18
- 229930182555 Penicillin Natural products 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 17
- AVKUERGKIZMTKX-NJBDSQKTSA-N ampicillin Chemical compound C1([C@@H](N)C(=O)N[C@H]2[C@H]3SC([C@@H](N3C2=O)C(O)=O)(C)C)=CC=CC=C1 AVKUERGKIZMTKX-NJBDSQKTSA-N 0.000 description 16
- 229960000723 ampicillin Drugs 0.000 description 16
- 230000002401 inhibitory effect Effects 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- 238000004809 thin layer chromatography Methods 0.000 description 16
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 15
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 15
- 238000002474 experimental method Methods 0.000 description 15
- 229940056360 penicillin g Drugs 0.000 description 15
- 150000002960 penicillins Chemical class 0.000 description 14
- 235000019371 penicillin G benzathine Nutrition 0.000 description 13
- 238000002360 preparation method Methods 0.000 description 13
- 239000011347 resin Substances 0.000 description 13
- 229920005989 resin Polymers 0.000 description 13
- 239000011734 sodium Substances 0.000 description 13
- 238000004587 chromatography analysis Methods 0.000 description 12
- 230000000694 effects Effects 0.000 description 12
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 11
- 235000019764 Soybean Meal Nutrition 0.000 description 11
- AGEZXYOZHKGVCM-UHFFFAOYSA-N benzyl bromide Chemical compound BrCC1=CC=CC=C1 AGEZXYOZHKGVCM-UHFFFAOYSA-N 0.000 description 11
- 150000003254 radicals Chemical class 0.000 description 11
- 239000004455 soybean meal Substances 0.000 description 11
- 108090000790 Enzymes Proteins 0.000 description 10
- 102000004190 Enzymes Human genes 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
- 239000008367 deionised water Substances 0.000 description 10
- 229910021641 deionized water Inorganic materials 0.000 description 10
- 239000000284 extract Substances 0.000 description 10
- 230000012010 growth Effects 0.000 description 10
- 238000005984 hydrogenation reaction Methods 0.000 description 10
- 229910052763 palladium Inorganic materials 0.000 description 10
- 239000007921 spray Substances 0.000 description 10
- 229920001817 Agar Polymers 0.000 description 9
- 229930186147 Cephalosporin Natural products 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- 241000588724 Escherichia coli Species 0.000 description 9
- 241000191967 Staphylococcus aureus Species 0.000 description 9
- 239000008272 agar Substances 0.000 description 9
- 239000001913 cellulose Substances 0.000 description 9
- 229920002678 cellulose Polymers 0.000 description 9
- 229940124587 cephalosporin Drugs 0.000 description 9
- 150000001780 cephalosporins Chemical class 0.000 description 9
- 239000013078 crystal Substances 0.000 description 9
- 238000000855 fermentation Methods 0.000 description 9
- 230000004151 fermentation Effects 0.000 description 9
- 229910003002 lithium salt Inorganic materials 0.000 description 9
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 8
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 8
- 239000002518 antifoaming agent Substances 0.000 description 8
- AZUFHGGGPUUXKI-FLFDDASRSA-N benzyl (2r,3z,5r)-3-(2-hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylate Chemical compound O=C([C@@H]1N2C(=O)C[C@H]2O\C1=C/CO)OCC1=CC=CC=C1 AZUFHGGGPUUXKI-FLFDDASRSA-N 0.000 description 8
- 235000010980 cellulose Nutrition 0.000 description 8
- 238000005119 centrifugation Methods 0.000 description 8
- 238000000605 extraction Methods 0.000 description 8
- 235000011187 glycerol Nutrition 0.000 description 8
- 238000004128 high performance liquid chromatography Methods 0.000 description 8
- 229910052708 sodium Inorganic materials 0.000 description 8
- 235000011121 sodium hydroxide Nutrition 0.000 description 8
- 229960005486 vaccine Drugs 0.000 description 8
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 7
- 238000005481 NMR spectroscopy Methods 0.000 description 7
- 235000008504 concentrate Nutrition 0.000 description 7
- 239000003112 inhibitor Substances 0.000 description 7
- 159000000002 lithium salts Chemical class 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- 150000004702 methyl esters Chemical class 0.000 description 7
- 244000005700 microbiome Species 0.000 description 7
- 238000005507 spraying Methods 0.000 description 7
- 229910001220 stainless steel Inorganic materials 0.000 description 7
- 239000010935 stainless steel Substances 0.000 description 7
- 239000006188 syrup Substances 0.000 description 7
- 235000020357 syrup Nutrition 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- 241000588769 Proteus <enterobacteria> Species 0.000 description 6
- 238000004458 analytical method Methods 0.000 description 6
- 230000001580 bacterial effect Effects 0.000 description 6
- 159000000007 calcium salts Chemical class 0.000 description 6
- CZTQZXZIADLWOZ-CRAIPNDOSA-N cefaloridine Chemical compound O=C([C@@H](NC(=O)CC=1SC=CC=1)[C@H]1SC2)N1C(C(=O)[O-])=C2C[N+]1=CC=CC=C1 CZTQZXZIADLWOZ-CRAIPNDOSA-N 0.000 description 6
- 239000000460 chlorine Substances 0.000 description 6
- 125000000068 chlorophenyl group Chemical group 0.000 description 6
- 239000008103 glucose Substances 0.000 description 6
- 230000007062 hydrolysis Effects 0.000 description 6
- 238000006460 hydrolysis reaction Methods 0.000 description 6
- 238000011081 inoculation Methods 0.000 description 6
- 238000002955 isolation Methods 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 230000002195 synergetic effect Effects 0.000 description 6
- 241000894006 Bacteria Species 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 5
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 5
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 description 5
- GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 5
- 241000191940 Staphylococcus Species 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- 239000006286 aqueous extract Substances 0.000 description 5
- 229940041514 candida albicans extract Drugs 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 239000012230 colorless oil Substances 0.000 description 5
- 239000012153 distilled water Substances 0.000 description 5
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 5
- 238000004816 paper chromatography Methods 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- 239000008399 tap water Substances 0.000 description 5
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
- 239000012138 yeast extract Substances 0.000 description 5
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 4
- 229920002307 Dextran Polymers 0.000 description 4
- 239000004375 Dextrin Substances 0.000 description 4
- 229920001353 Dextrin Polymers 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical class NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 4
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 150000003863 ammonium salts Chemical class 0.000 description 4
- 239000003242 anti bacterial agent Substances 0.000 description 4
- 229940088710 antibiotic agent Drugs 0.000 description 4
- 238000009395 breeding Methods 0.000 description 4
- 230000001488 breeding effect Effects 0.000 description 4
- 239000003610 charcoal Substances 0.000 description 4
- 229920001429 chelating resin Polymers 0.000 description 4
- 235000019425 dextrin Nutrition 0.000 description 4
- 238000010828 elution Methods 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 239000012535 impurity Substances 0.000 description 4
- 239000011777 magnesium Substances 0.000 description 4
- 159000000003 magnesium salts Chemical class 0.000 description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 description 4
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 239000001103 potassium chloride Substances 0.000 description 4
- 235000011164 potassium chloride Nutrition 0.000 description 4
- 239000002244 precipitate Substances 0.000 description 4
- 238000000746 purification Methods 0.000 description 4
- 229920006395 saturated elastomer Polymers 0.000 description 4
- SQGYOTSLMSWVJD-UHFFFAOYSA-N silver(1+) nitrate Chemical compound [Ag+].[O-]N(=O)=O SQGYOTSLMSWVJD-UHFFFAOYSA-N 0.000 description 4
- VWDWKYIASSYTQR-UHFFFAOYSA-N sodium nitrate Chemical compound [Na+].[O-][N+]([O-])=O VWDWKYIASSYTQR-UHFFFAOYSA-N 0.000 description 4
- WOGMLDNCNBLDCA-JSYANWSFSA-M sodium;(2r,3z,5r)-3-(2-hydroxyethylidene)-7-oxo-4-oxa-1-azabicyclo[3.2.0]heptane-2-carboxylate Chemical compound [Na+].[O-]C(=O)[C@H]1C(=C/CO)/O[C@@H]2CC(=O)N21 WOGMLDNCNBLDCA-JSYANWSFSA-M 0.000 description 4
- 239000011877 solvent mixture Substances 0.000 description 4
- 238000001228 spectrum Methods 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
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- 238000005406 washing Methods 0.000 description 4
- GUBGYTABKSRVRQ-WFVLMXAXSA-N DEAE-cellulose Chemical compound OC1C(O)C(O)C(CO)O[C@H]1O[C@@H]1C(CO)OC(O)C(O)C1O GUBGYTABKSRVRQ-WFVLMXAXSA-N 0.000 description 3
- 230000005526 G1 to G0 transition Effects 0.000 description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- 229940123930 Lactamase inhibitor Drugs 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical class [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 3
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 3
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 3
- 239000001888 Peptone Substances 0.000 description 3
- 108010080698 Peptones Proteins 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 3
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 3
- 229920002472 Starch Polymers 0.000 description 3
- 241000212749 Zesius chrysomallus Species 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 230000000721 bacterilogical effect Effects 0.000 description 3
- 239000007853 buffer solution Substances 0.000 description 3
- FPPNZSSZRUTDAP-UWFZAAFLSA-N carbenicillin Chemical compound N([C@H]1[C@H]2SC([C@@H](N2C1=O)C(O)=O)(C)C)C(=O)C(C(O)=O)C1=CC=CC=C1 FPPNZSSZRUTDAP-UWFZAAFLSA-N 0.000 description 3
- 229960003669 carbenicillin Drugs 0.000 description 3
- 239000001569 carbon dioxide Substances 0.000 description 3
- 229910002092 carbon dioxide Inorganic materials 0.000 description 3
- 238000004140 cleaning Methods 0.000 description 3
- 238000004440 column chromatography Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000005886 esterification reaction Methods 0.000 description 3
- 238000004108 freeze drying Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 230000002779 inactivation Effects 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 238000005342 ion exchange Methods 0.000 description 3
- 230000007246 mechanism Effects 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 3
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/18—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms containing at least two hetero rings condensed among themselves or condensed with a common carbocyclic ring system, e.g. rifamycin
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P17/00—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms
- C12P17/18—Preparation of heterocyclic carbon compounds with only O, N, S, Se or Te as ring hetero atoms containing at least two hetero rings condensed among themselves or condensed with a common carbocyclic ring system, e.g. rifamycin
- C12P17/188—Heterocyclic compound containing in the condensed system at least one hetero ring having nitrogen atoms and oxygen atoms as the only ring heteroatoms
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/42—Oxazoles
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/41—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having five-membered rings with two or more ring hetero atoms, at least one of which being nitrogen, e.g. tetrazole
- A61K31/425—Thiazoles
- A61K31/429—Thiazoles condensed with heterocyclic ring systems
- A61K31/43—Compounds containing 4-thia-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula, e.g. penicillins, penems
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/04—Antibacterial agents
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D503/00—Heterocyclic compounds containing 4-oxa-1-azabicyclo [3.2.0] heptane ring systems, i.e. compounds containing a ring system of the formula:, e.g. oxapenicillins, clavulanic acid derivatives; Such ring systems being further condensed, e.g. 2,3-condensed with an oxygen-, nitrogen- or sulfur-containing hetero ring
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12N—MICROORGANISMS OR ENZYMES; COMPOSITIONS THEREOF; PROPAGATING, PRESERVING, OR MAINTAINING MICROORGANISMS; MUTATION OR GENETIC ENGINEERING; CULTURE MEDIA
- C12N1/00—Microorganisms, e.g. protozoa; Compositions thereof; Processes of propagating, maintaining or preserving microorganisms or compositions thereof; Processes of preparing or isolating a composition containing a microorganism; Culture media therefor
- C12N1/20—Bacteria; Culture media therefor
- C12N1/205—Bacterial isolates
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12R—INDEXING SCHEME ASSOCIATED WITH SUBCLASSES C12C - C12Q, RELATING TO MICROORGANISMS
- C12R2001/00—Microorganisms ; Processes using microorganisms
- C12R2001/01—Bacteria or Actinomycetales ; using bacteria or Actinomycetales
- C12R2001/465—Streptomyces
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02A—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE
- Y02A50/00—TECHNOLOGIES FOR ADAPTATION TO CLIMATE CHANGE in human health protection, e.g. against extreme weather
- Y02A50/30—Against vector-borne diseases, e.g. mosquito-borne, fly-borne, tick-borne or waterborne diseases whose impact is exacerbated by climate change
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- General Health & Medical Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Medicinal Chemistry (AREA)
- Biotechnology (AREA)
- Genetics & Genomics (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Biochemistry (AREA)
- General Engineering & Computer Science (AREA)
- Microbiology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Epidemiology (AREA)
- Tropical Medicine & Parasitology (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Communicable Diseases (AREA)
- Oncology (AREA)
- Virology (AREA)
- Biomedical Technology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Enzymes And Modification Thereof (AREA)
- Micro-Organisms Or Cultivation Processes Thereof (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB17410/74A GB1508977A (en) | 1974-04-20 | 1974-04-20 | Beta-lactam antibiotic from streptomyces clavuligerus |
| GB2771574 | 1974-06-21 | ||
| GB4365174 | 1974-10-09 | ||
| GB5352574 | 1974-12-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2560074C2 true DE2560074C2 (de) | 1985-03-28 |
Family
ID=27448389
Family Applications (4)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2560074A Expired DE2560074C2 (de) | 1974-04-20 | 1975-04-18 | Verfahren zur Gewinnung von Clavulansäure und deren Salze |
| DE2517316A Expired DE2517316C2 (de) | 1974-04-20 | 1975-04-18 | Clavulansäure und deren Salze und diese Verbindungen enthaltende Arzneimittel |
| DE2559411A Expired DE2559411C2 (de) | 1974-04-20 | 1975-04-18 | Verwendung von Clavulansäure |
| DE19752559410 Ceased DE2559410A1 (de) | 1974-04-20 | 1975-04-18 | Ester der clavulansaeure, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
Family Applications After (3)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2517316A Expired DE2517316C2 (de) | 1974-04-20 | 1975-04-18 | Clavulansäure und deren Salze und diese Verbindungen enthaltende Arzneimittel |
| DE2559411A Expired DE2559411C2 (de) | 1974-04-20 | 1975-04-18 | Verwendung von Clavulansäure |
| DE19752559410 Ceased DE2559410A1 (de) | 1974-04-20 | 1975-04-18 | Ester der clavulansaeure, verfahren zu ihrer herstellung und diese verbindungen enthaltende arzneimittel |
Country Status (26)
Families Citing this family (94)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NZ177159A (en) * | 1974-04-20 | 1978-03-06 | Beecham Group Ltd | Clavulanic acid, salts, esters and preparation thereof from streptomyces clavuligerus: pharmaceutical compositions |
| DE2604697A1 (de) * | 1975-02-07 | 1976-08-19 | Glaxo Lab Ltd | Antibiotika |
| JPS596796Y2 (ja) * | 1975-04-04 | 1984-03-01 | 株式会社東芝 | 脱水兼用洗濯機 |
| US6051703C1 (en) * | 1975-04-17 | 2001-10-06 | Smithkline Beecham Plc | Purified clavulanic acid and salts thereof |
| US6218380B1 (en) * | 1975-04-17 | 2001-04-17 | Smithkline Beecham P.L.C. | Pharmaceutical compositions |
| GB1563103A (en) * | 1975-10-13 | 1980-03-19 | Beecham Group Ltd | Process for the preparation of clavulanic acid |
| US4230622A (en) * | 1975-12-17 | 1980-10-28 | Glaxo Laboratories Limited | Halogen derivatives of clavulaic acid |
| GB1515241A (en) * | 1976-01-27 | 1978-06-21 | Beecham Group Ltd | Beta-lactam antibiotics |
| DE2725690A1 (de) * | 1976-06-08 | 1977-12-22 | Glaxo Lab Ltd | Neue clavulansaeurederivate, verfahren zu deren herstellung und diese enthaltende zusammensetzungen |
| GB1562802A (en) * | 1976-06-26 | 1980-03-19 | Beecham Group Ltd | Pharmaceutical compositions containing containing clavulanic acid |
| GB1562902A (en) * | 1976-06-30 | 1980-03-19 | Beecham Group Ltd | Pharmaceutical compositions containing clavulanic acid |
| GB1578739A (en) * | 1976-07-23 | 1980-11-05 | Beecham Group Ltd | Amine salts of clavulanic acid methods for their preparation and compositions containing them |
| GB1594001A (en) * | 1977-03-16 | 1981-07-30 | Beecham Group Ltd | Pellets suitable for use in the testing of microorganisms |
| GB1582884A (en) * | 1977-05-19 | 1981-01-14 | Beecham Group Ltd | Clavulanic acid derivatives their preparation and use |
| DE2912511C2 (de) * | 1977-06-07 | 1982-06-24 | Pfizer Inc., 10017 New York, N.Y. | Pharmazeutische Zusammensetzung, enthaltend Penicillansäure |
| JO984B1 (en) * | 1977-10-11 | 1979-12-01 | بيتشام غروب ليمتد | A dry pharmaceutical compound with a suitable dosage unit for oral administration |
| JPS54126735A (en) * | 1978-03-24 | 1979-10-02 | Toyama Chem Co Ltd | Bactericidal composition for medical use |
| EP0008905B1 (en) * | 1978-09-06 | 1983-02-16 | Beecham Group Plc | Pharmaceutical compositions containing two beta-lactam derivatives |
| JPS5545906U (enrdf_load_stackoverflow) * | 1978-09-21 | 1980-03-26 | ||
| US4202819A (en) * | 1979-05-04 | 1980-05-13 | Hoffman-La Roche Inc. | 2-(3-Alanyl)clavam antibiotic |
| DK330880A (da) * | 1979-08-03 | 1981-02-04 | Beecham Group Ltd | Fremgangsmaade til fremstilling af clavulansyrederivater |
| DE3063683D1 (en) * | 1979-08-24 | 1983-07-14 | Beecham Group Plc | Amine salt of clavulanic acid, its preparation and use |
| NZ199061A (en) * | 1980-12-09 | 1984-10-19 | Beecham Group Ltd | 9-(n-tetrazolyl)-deoxyclavulanic acids,salts,esters,and pharmaceutical compositions |
| US4562182A (en) * | 1980-12-23 | 1985-12-31 | Beecham Group P.L.C. | Compounds containing beta-lactams |
| US4684643A (en) * | 1983-08-22 | 1987-08-04 | Eli Lilly And Company | Pharmaceutical compositions for storage in plastic containers and process therefor |
| US4533542A (en) * | 1983-08-22 | 1985-08-06 | Eli Lilly And Company | Pharmaceutical compositions for storage in plastic containers and process therefor |
| IT1207982B (it) * | 1983-10-07 | 1989-06-01 | Lisapharma Spa | Composizioni farmaceutiche adattivita' antibiotica. |
| JPS6155889A (ja) * | 1984-08-28 | 1986-03-20 | 松下電器産業株式会社 | 高周波加熱装置 |
| US4757066A (en) * | 1984-10-15 | 1988-07-12 | Sankyo Company Limited | Composition containing a penem or carbapenem antibiotic and the use of the same |
| DE3725375A1 (de) * | 1987-07-31 | 1989-02-09 | Bayer Ag | Stabile oxapenem-3-carbonsaeuren |
| GB9009446D0 (en) * | 1990-04-26 | 1990-06-20 | Beecham Group Plc | Veterinary composition |
| DE4027928A1 (de) * | 1990-09-04 | 1992-03-05 | Bayer Ag | Neue 2-tert.substituierte methyl-oxapenem-3-carbonsaeuren und -ester, verfahren zu ihrer herstellung und ihre verwendung |
| DE4030706A1 (de) * | 1990-09-28 | 1992-04-02 | Bayer Ag | Neue 3-substituierte cephalosporine, verfahren zu ihrer herstellung und ihre verwendung als arzneimittel |
| GB9201639D0 (en) * | 1992-01-25 | 1992-03-11 | Smithkline Beecham Plc | Pharmaceutical formulations |
| AT400033B (de) * | 1992-03-10 | 1995-09-25 | Biochemie Gmbh | Neues verfahren zur isolierung und reinigung von clavulansäure und zur herstellung von pharmakologisch verträglichen salzen derselben |
| AT399155B (de) * | 1992-03-26 | 1995-03-27 | Lek Tovarna Farmacevtskih | Neue alkylendiammonium-diclavulanat-derivate, verfahren zu deren herstellung sowie deren verwendung |
| AU5863894A (en) * | 1993-01-22 | 1994-08-15 | Smithkline Beecham Plc | Pharmaceutical formulations comprising clavulanic acid alone or in combination with other beta-lactam antibiotics |
| US5821364A (en) * | 1993-03-26 | 1998-10-13 | Gist-Brocades N.V. | Diamine salts of clavulanic acid |
| US5760218A (en) * | 1993-03-26 | 1998-06-02 | Gist-Brocades N.V. | Diamine salts of clavulanic acid |
| RO112113B1 (ro) * | 1993-03-26 | 1997-05-30 | Gist Brocades Nv | Saruri diaminice ale acidului clavulanic si procedeu pentru prepararea acestora |
| US5741903A (en) * | 1993-03-26 | 1998-04-21 | Gist-Brocades N.V. | Diamine salts for purification of clavulanic acid |
| US20030219867A1 (en) * | 1993-07-24 | 2003-11-27 | Smithkline Beecham Plc | Clavulanic acid dehydrogenase, preparation and use for the production of clavulanic acid |
| GB9315393D0 (en) * | 1993-07-24 | 1993-09-08 | Smithkline Beecham Plc | Novel product |
| SI9400107A (en) * | 1994-03-02 | 1995-10-31 | Lek Tovarna Farmacevtskih | New process of the isolation of clavulanic acid and its pharmaceutical salts from fermented broth of streptomyces sp.p 6621 ferm p 2804. |
| US20030109503A1 (en) * | 1995-06-06 | 2003-06-12 | Smithkline Beecham P.L.C. | Pharmaceutical formulations comprising clavulanic acid alone or in combination with other beta-lactam antibiotics |
| GB9515809D0 (en) * | 1995-08-02 | 1995-10-04 | Smithkline Beecham Plc | Process |
| SI9500265A1 (en) | 1995-08-28 | 1997-02-28 | Lek Tovarna Farmacevtskih | Process for purification of the aqueous fermented broth filtrate of streptomyces sp. p 6621 ferm p 2804 by ultrafiltration |
| HUP9901437A3 (en) * | 1995-09-07 | 2000-03-28 | Smithkline Beecham Plc | Pharmaceutical formulation, containing amoxycillin and clavulanate |
| AT403375B (de) * | 1995-11-15 | 1998-01-26 | Biochemie Gmbh | Verfahren zur fällung von alkalisalzen der clavulansäure |
| US20030124187A1 (en) * | 1997-02-14 | 2003-07-03 | Smithkline Beecham Laboratoires Pharmaceutiques, | Pharmaceutical formulations comprising amoxycillin and clavulanate |
| EP2256211A3 (en) * | 1997-02-20 | 2011-02-16 | DSM IP Assets B.V. | Fermentative production of valuable compounds on an industrial scale using chemically defined media |
| AR015825A1 (es) * | 1997-05-28 | 2001-05-30 | Gist Brocades Bv | Produccion fermentativa de acido clavulanico bajo condiciones controladas de fosfato |
| WO2000001840A1 (en) * | 1998-07-03 | 2000-01-13 | Dsm N.V. | Fermentation process to produce clavulanic acid at a low concentration of free amino acids |
| US6878386B1 (en) | 1999-04-13 | 2005-04-12 | Beecham Pharmaceuticals (Pte) Limited | Method of treating a bacterial infection comprising amoxycillin and potassium clavulanate |
| US6294199B1 (en) * | 1999-04-13 | 2001-09-25 | Beecham Pharmaceuticals (Pte) Limited | Method of treating a bacterial infection comprising administering amoxycillin |
| US7250176B1 (en) * | 1999-04-13 | 2007-07-31 | Beecham Pharmaceuticals (Pte) Limited | Method of treating a bacterial infection |
| US6544555B2 (en) | 2000-02-24 | 2003-04-08 | Advancis Pharmaceutical Corp. | Antibiotic product, use and formulation thereof |
| US6565882B2 (en) | 2000-02-24 | 2003-05-20 | Advancis Pharmaceutical Corp | Antibiotic composition with inhibitor |
| US6756057B2 (en) | 2000-10-12 | 2004-06-29 | Beecham Pharmaceuticals (Pte) Limited | Amoxicillin and potassium clavulanate dosage form |
| AU2001292185A1 (en) | 2000-10-12 | 2002-04-22 | Beecham Pharmaceuticals (Pte) Limited | Formulation containing amoxicillin |
| US6541014B2 (en) | 2000-10-13 | 2003-04-01 | Advancis Pharmaceutical Corp. | Antiviral product, use and formulation thereof |
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Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2517316C2 (de) * | 1974-04-20 | 1985-03-07 | Beecham Group Ltd., Brentford, Middlesex | Clavulansäure und deren Salze und diese Verbindungen enthaltende Arzneimittel |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3801464A (en) | 1972-02-09 | 1974-04-02 | Lilly Co Eli | Antibiotic a16886 and process for production thereof |
| US4123540A (en) * | 1974-12-18 | 1978-10-31 | Beecham Group Limited | Isoclavulanic acid as an antibacterial and a β-lactamase inhibitor |
| US4140764A (en) * | 1974-12-18 | 1979-02-20 | Beecham Group Limited | β-Lactamase inhibitors and process for their preparation |
| DE2604697A1 (de) * | 1975-02-07 | 1976-08-19 | Glaxo Lab Ltd | Antibiotika |
| US4144242A (en) * | 1975-02-07 | 1979-03-13 | Glaxo Laboratories Limited | Process for the purification of clavulanic acid |
| JO984B1 (en) * | 1977-10-11 | 1979-12-01 | بيتشام غروب ليمتد | A dry pharmaceutical compound with a suitable dosage unit for oral administration |
-
1975
- 1975-04-08 NZ NZ177159A patent/NZ177159A/xx unknown
- 1975-04-08 IE IE792/75A patent/IE41109B1/xx not_active IP Right Cessation
- 1975-04-09 YU YU908/75A patent/YU39941B/xx unknown
- 1975-04-11 FR FR7511344A patent/FR2267778B1/fr not_active Expired
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- 1975-04-14 IL IL47087A patent/IL47087A/xx unknown
- 1975-04-14 IN IN743/CAL/75A patent/IN140042B/en unknown
- 1975-04-16 FI FI751133A patent/FI54144C/fi not_active IP Right Cessation
- 1975-04-18 DE DE2560074A patent/DE2560074C2/de not_active Expired
- 1975-04-18 DD DD7500193531A patent/DD132297A5/xx unknown
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- 1975-04-18 DE DE2517316A patent/DE2517316C2/de not_active Expired
- 1975-04-18 NO NO751407A patent/NO145247C/no unknown
- 1975-04-18 AR AR258435A patent/AR206627A1/es active
- 1975-04-18 SE SE7504541A patent/SE422063B/xx not_active IP Right Cessation
- 1975-04-18 DK DK167275AA patent/DK141254B/da not_active IP Right Cessation
- 1975-04-18 DE DE2559411A patent/DE2559411C2/de not_active Expired
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- 1975-04-18 LU LU72322A patent/LU72322A1/xx unknown
- 1975-04-18 NL NL7504621.A patent/NL163824C/xx not_active IP Right Cessation
- 1975-04-18 DE DE19752559410 patent/DE2559410A1/de not_active Ceased
- 1975-04-19 OA OA55480A patent/OA05203A/xx unknown
- 1975-04-19 RO RO7595311A patent/RO77320A/ro unknown
- 1975-04-19 RO RO7582037A patent/RO69984A/ro unknown
- 1975-04-19 JP JP50048087A patent/JPS5246957B2/ja not_active Expired
- 1975-04-19 JP JP50048086A patent/JPS521996B2/ja not_active Expired
- 1975-04-21 PH PH17082A patent/PH16474A/en unknown
- 1975-04-21 CH CH506075A patent/CH629252A5/de not_active IP Right Cessation
- 1975-11-28 AR AR261404A patent/AR219050A1/es active
- 1975-11-28 AR AR261403A patent/AR216430A1/es active
-
1976
- 1976-09-24 US US06/726,224 patent/US4427690A/en not_active Expired - Lifetime
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1977
- 1977-04-05 JP JP4026177A patent/JPS533590A/ja active Pending
- 1977-04-05 JP JP4025877A patent/JPS532495A/ja active Granted
- 1977-04-05 JP JP4025777A patent/JPS532494A/ja active Granted
- 1977-04-05 JP JP4026077A patent/JPS533589A/ja active Granted
- 1977-04-05 JP JP4025977A patent/JPS533588A/ja active Granted
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1978
- 1978-07-13 US US05/924,174 patent/US4556559A/en not_active Expired - Lifetime
- 1978-10-27 SE SE7811201A patent/SE446687B/sv not_active IP Right Cessation
- 1978-10-27 SE SE7811200A patent/SE435286B/sv not_active IP Right Cessation
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- 1978-10-27 SE SE7811202A patent/SE435287B/sv not_active IP Right Cessation
-
1979
- 1979-06-12 NO NO791956A patent/NO150838C/no unknown
-
1980
- 1980-06-20 NO NO801852A patent/NO801852L/no unknown
- 1980-08-29 KE KE3076A patent/KE3076A/xx unknown
- 1980-09-25 HK HK547/80A patent/HK54780A/xx unknown
- 1980-12-22 CH CH947280A patent/CH630631A5/de not_active IP Right Cessation
-
1981
- 1981-06-09 US US06/272,030 patent/US4526783A/en not_active Expired - Lifetime
- 1981-10-02 SE SE8105829A patent/SE453600B/sv not_active IP Right Cessation
- 1981-11-23 YU YU2744/81A patent/YU42745B/xx unknown
- 1981-11-23 YU YU2743/81A patent/YU42744B/xx unknown
- 1981-12-03 US US06/327,253 patent/US4525352A/en not_active Expired - Lifetime
- 1981-12-14 US US06330456 patent/US4560552C1/en not_active Expired - Lifetime
- 1981-12-30 MY MY195/81A patent/MY8100195A/xx unknown
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1983
- 1983-11-16 SE SE8306328A patent/SE8306328D0/xx unknown
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1986
- 1986-12-16 SE SE8605405A patent/SE8605405D0/xx unknown
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2517316C2 (de) * | 1974-04-20 | 1985-03-07 | Beecham Group Ltd., Brentford, Middlesex | Clavulansäure und deren Salze und diese Verbindungen enthaltende Arzneimittel |
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